Please, Mr Jailer
by Crazychicke
Summary: Based on the movie Cry-Baby with Johnny Depp and adapted for Steroline. It's senior year and Caroline is happy, or so she thinks, dating Tyler Lockwood. Her life is turned upside down when she meets Stefan, a Drape, who gets under her skin & shows her what life on the other side is really like. Featuring. Maggie Forbes. Couples: Steroline, Sarah/Matt, Debekah & implied Tylena.


**Disclaimer: Not mine as much as I wish it. A/N: Cry-baby is one of my favourite musicals, I found quite by accident because it had Johnny Depp in it, among others. It's set in the 1950s. :)**

**Please, Mr Jailer**

Caroline Forbes waited in line for her vaccination, gripping her hands together while her boyfriend, Tyler Lockwood, hugged her from behind. There were shouts coming from behind them, and the school nurses shoved someone to the front of the queue. It was a Drape, Stefan Salvatore, who had tried to escape the needle. He was, what her Grams would have called, a 'ruffian', because of his disregard for rules.

Stefan didn't notice Caroline, despite knocking into her. He stumbled up the stairs to his empty seat in front of their senior year. He struggled left and right until the nurses turned down his jacket. When they beckoned her to the other chair, Caroline swallowed, nervous to receive the same treatment. Stefan's sweet blue eyes called out to her when she climbed the stairs, taking her seat.

She received her injection with a wince and was both surprised and sympathetic when witnessing one tear fall down Stefan's cheek. Caroline picked up her books, ignoring, Tyler's teasing and went to talk to Stefan outside. She felt a significant pull towards him, and when Stefan looked over his shoulder, he grinned when he saw her following him. "Hey!" she said, watching him put an arm around a dark-haired girl who happened to be pregnant.

"Hey," he reached for his friends' cigarette, offering it to her, first. She shook her head, eyes wide when he flicked open his lighter. "This is my sister, Sarah," Stefan said, taking a drag on his cigarette. Caroline shook her hand. Stefan gestured at a frowning girl and her boyfriend. "That's Rebekah and my brother Damon," Caroline nodded. "And that's Katherine," he added when Caroline turned her attention to a third girl sucking on a lollipop.

Caroline took a deep breath: "I was wondering," Stefan listened, propping his foot against his car door. "If you'd like to join us at my Grams' talent show tonight?" Rebekah smirked and Damon chuckled into her shoulder. "It's to raise money for student amenities," she said, unsure what the joke was. Tyler arrived, kissing her cheek. She knew he would rather drop dead than extend an invitation to her new friends, but she was the hostess, and it was still her party.

"We've got band practice down by the waterhole. You should come," Stefan said, putting out his cigarette with the heel of his shoe. Caroline was about to say 'she'd think about it' when Tyler interrupted: "_Honey_, your Grams is here to pick us up." He looked up at them and said: "If you'll excuse us, we've a charity event to host." Caroline shook her wrist free from Tyler's grip, and headed towards the car, climbing into the back seat without his help, and hugging her text-books.

Maggie Forbes rested her hands on the wheel, eyeing the 'ruffians' in her rear-vision mirror. "There's evil in their blood," she hissed, reversing the car and getting an agreeable nod from Tyler.

"Those 'Drapes' are bad news, Care. It's too late to try and befriend them. They're never going to change. I promised your Grams I'd look after you," he said over his shoulder. Maggie beamed indicating she approved of them going steady. Caroline frowned, wanting more from life.

* * *

Stefan sat in the driver's seat of his black car, playing with the jazz stations on the radio while Sarah, picked up her unfinished knitting, pulling the thread over the needle. "I think Cry-Baby's got a girlfriend..." she teased. Damon smirked, his arm around Rebekah, kissing her earlobe and getting turned on by her constant moans. Katherine picked the wrapper off another lollipop, this time, grape flavoured, but seemed interested by the current conversation.

Stefan rolled his eyes, but a smile had appeared on his lips. He ran his hand through his thick hair, and sang along to the radio. "Steffy and Caroline, sitting in a tree," Damon began, laughing when Stefan's ears grew red. Rebekah joined in. "K.I.S.S.I.N.G!" They laughed, and Sarah reached out to shake his shoulder. "She's a scrape," she shrugged. "Part square, part drape." Stefan sighed, steering the car in the opposite direction, unable to get Caroline Forbes out of his head.

* * *

When Caroline arrived to her Grams' house, she refused Tyler's helpful hand, marching up to her room to see a white dress laid out on her bed; a white lace thing that reached her ankles, and was pretty, but also plain. Caroline pulled on some white gloves to match with a sigh, and recited her favourite song, trying to put Stefan out of her mind. She couldn't concentrate during the entire talent show, not even singing her favourite song could perk up her spirits. It wasn't until the unmistakeable roar of a _Harley Davidson_ interrupted Tyler's juggling performance and made him fumble his last catch, did Caroline leave her seat to look out the window.

"Caroline!" Butterflies erupted in her chest at the sight of Stefan sitting on his bike, a helmet dangling from the handlebars, grinning like a fool. "I'm going to sing tonight, and I thought you'd want to hear us." Stefan dismounted, walking to her door, his leather jacket rustling when he walked. Maggie grimaced, disapproving of the idea. Tyler took it upon himself to protect them all, throwing open the front door and running straight at Stefan. Caroline was so mad she tried to stop herself from shaking by clenching her fists together.

"How dare you hit him, you don't own me! I have the right to hear Stefan sing!" Maggie hustled back the witnesses, telling them to keep going with the festivities. Tyler shook his bruised hand, proud of himself and thinking she was overreacting. "Don't get worked up, _honey_. The punk got what he deserved." Caroline held her breath, watching Stefan get up and punch Tyler. Before she knew what had happened, he reached for her hand and Maggie stepped over Tyler anxious for her Caroline's safety.

"It's ok, Mrs Forbes, I'll take good care of her and I promise you, I'll bring her home, safe and sound." Caroline sent a pleading look to her Grams to trust her. "What if you get your dress dirty?" Maggie frowned, admiring the intricate lace but Caroline didn't give a stuff about her dress, she craved an adventure, anything to escape Tyler. Maggie sighed, seeing it in Caroline's eyes, the same spark she used to have when she was young. Caroline hugged Maggie and she climbed onto Stefan's bike.

Caroline held onto his waist, resting her head on his shoulder. "You just look square, but beneath it all, I think you're just hip," Stefan grinned, driving them down to the waterhole. He parked the bike at the top of the hill and Caroline saw they had a welcome party. She felt self-conscious as Sarah, Rebekah and Katherine, met them. "You need a new look!" Sarah said, taking in Caroline's debutante dress and shaking her head at the gloves.

Rebekah agreed. "Don't you got tits, stick them out for God's Sake!" showing off her own. Katherine grinned."I think I've an idea!" she said. Caroline heard Stefan and Damon testing the microphones on stage while Katherine gave her some new leather pants, tying a red scarf through its belt. Rebekah smirked, adjusting Caroline's yellow top, making sure to lift her breasts up while Sarah brushed Caroline's hair into a wavy 1950s do. "Now you're a Drape," Sarah grinned, smoothing her hand over her pregnant stomach. Caroline felt proud to be, taking Sarah's hand and praying Stefan approved.

Stefan pulled back the curtain. Caroline brushed her hands over her pants, liking the way they made her legs look so slim. She smiled in response to Stefan and Damon's gawking expressions. Damon gave Rebekah a sweet kiss and picked up his double bass. Sarah spun her drumstick in her hand and Katherine yawned, dinging her triangle. Rebekah blew a few notes of her saxophone while Stefan tore his eyes from Caroline, and tuned his guitar.

"Alright, ladies and gentlemen!" Stefan announced to the crowd. "Tonight, we've a special guest all the way from Mystic Falls, and I want you to make her feel welcome!" He grinned. "Miss Caroline Forbes, everyone!" Caroline gave them a wave, standing awkwardly beside him, but excited to be invited on stage. She felt anxious when the music began to play with faster tempos than she was used to, but he encouraged the crowd with a wave of his arm and they continued to cheer her on.

_"Well I'm a lonely king who needs a queen, yeah, you're the sweetest hunk of sugar that I've ever seen. I got a rainbow crown for you. Well, if I had your love, all I'd do is cry baby blues!"_

Caroline swayed from side to side, grinning whenever Stefan winked at her between lyrics. She cheered with the rest of the crowd when Damon, Rebekah and Sarah had their instrument solos and frowned when one girl in the crowd removed her knickers and threw them at Stefan, giving him a wink. _Who was she? An ex-girlfriend? _Caroline thought, but soon Stefan had kicked them off the stage and only had eyes for her, that she soon forgot about the other girl.

Sarah flicked her long hair over her shoulder, catching a Square's eye in return, and smiling when he looked at her like there was nobody more beautiful. She waved to the front row, where her four-year old twins, Liv and Luke stood, dancing with her mother, Lily Salvatore. She blew them each a kiss. Stefan grinned into the mic and Caroline laughed when she realized how much fun she was having.

_"She's the queen, she's the queen..." _It wasn't just Stefan singing now, the rest of the band were grinning and looking at her, and she knew this was her moment to shine. She began very faintly but eventually gathered her courage. "_Well, let people talk, I don't care... Let me prove to you, Daddy, that I ain't no square...!" _The crowd loved her, except for, Caroline noticed, the girl without any knickers, who pouted at the back of the mosh pit.

Caroline and Stefan grinned, sweat mingled in their fringes. "_You'll be my queen and I'll be your king. Cry-baby, cry, Cry-baby cryyyyy!"_ and they stared into each other's eyes, breathless but with their adrenaline pumping. It took Katherine dinging her triangle in their faces to pull them back to reality.

* * *

Later, after being introduced to Stefan's mother and a BBQ dinner, the band split up for some privacy. Stefan took Caroline's hand and showed her what they did for entertainment. "I've never given a French kiss before..." she whispered, sitting on a picnic rug and liking how Stefan was caressing her hand. "Just try it, if you don't like it, I promise I'll stop," he was so gentle and so romantic she trusted him more than she had trusted any boy. They closed their eyes, and she followed his lead, grazing his bottom lip with her tongue. His hands slipped beneath her top and they fell back onto the rug. "Oh Cry-Baby, you're fingers feel so good!" she cried.

Stefan smirked against her neck, pressing his lips over her chest and then back to her mouth, his hand began to unbutton the top of her pants. She stopped him. "I want to let you but I can't... for my parent's sake, Cry-baby they're both dead, I'm an orphan.." Stefan lay beside her. "My father was the Alphabet Bomber, they electrocuted him to death. They would have had my mama too, if she hadn't have faked her death..." There was a bolt of lightning causing a branch above them to snap.

Caroline screamed. Stefan pushed her off the rug, rising to his feet with a mad look on his face.

"Lightning makes me insane! Because of what they did to my dad, I am forced do something rotten for their sake and I cry for my sins: just one salty tear, is all they're going to get from me!" Caroline held onto his shoulders, keeping him calm and watching that one special tear dribble down his cheek. She had never felt more alive in her life and she wanted to show him she wasn't going anywhere. She licked that one tear. "Come to me, whenever you want, and I won't let you lose control," she whispered and then kissed him, the way he had shown her.

* * *

"DRAPES CAN SUCK IT!" Yells alerted them to the top of the hill where Stefan's motorbike had been set alight and now zoomed towards them. Caroline glared at their ring leader, her ex-boyfriend. Lily Salvatore told them to stay calm, and Caroline only just then noticed her hat had a dead-duck on top of it. The twins weren't fazed at all, clapping when the bike hit the stage and the whole thing caught fire, disturbing all the couples that had been slow dancing to the music from the Duke-box.

Sarah and Matt Donovan pulled apart from their embrace, and she looked around for her kids, worried for their safety. Stefan pulled Caroline along, hearing sirens wailing and trying to help the others from the coming onslaught. Sarah jabbed a Square in the eye with her drum stick, while Matt punched him out. Rebekah and Damon were also a team, tripping up the Squares and exchanging a baseball bat between them as a weapon. Lily Salvatore slammed a garbage bin over the top of a Square who seriously misjudged her strength. Katherine pulled up her stockings and powdered her nose, before punching a Square in the face, and cleaning her muddy Gucci heels on his shirt.

Caroline gaped at the destruction around her and felt furious by the fact that Tyler had started it all.

Tyler dodged the end of Damon's baseball bat and Stefan waited until he was close enough before punching him in the nose. She stopped Stefan from losing control, telling him to go help the others while she knelt beside her smug ex, aware of how dirty her dress was. "What are you doing here? I came willingly, remember?" Tyler sighed, blood dribbling from his clenched hand. She gave him a hanky to stop the blood flow. "He's just using you," Tyler said. "He doesn't love you like I do."

Caroline sighed. "Tyler, I-" she looked up to see the waterhole swarming with police and all the Drapes being rounded up, including Stefan. She left Tyler on the ground to explain there had been some kind of misunderstanding and as she pulled on the officer's sleeve, begging for him to listen he shoved her off so that she fell in the mud. Tyler helped her stand and Caroline stumbled back in shock when the girl with no knickers shouted to a journalist: 'Cry-Baby's the father of my unborn child!' Caroline stared up at Stefan as he was taken away, and felt her dreams shattering around her.

The next morning, Caroline read the newspaper for information on Stefan's court case. She hadn't touched her toast and prayed there'd be confirmation to say whether or not Stefan had knocked up Elena, like she'd implied. He had been given a lesser sentence since he classified as a juvenile delinquent and Tyler and his pals only escaped because they had good lawyers. Maggie cleared her throat. "Does that sound like a marching band?"

Maggie knew what Caroline didn't, that Tyler would be proposing, and had organized an extravagant event to win back her already broken heart. Maggie wanted what was best for her granddaughter, but even the sound of a parade didn't perk up her spirits like it used to. Maggie glanced at the photograph of Stefan at court, with an inset of the twins, who had been put into an orphanage until their mother had carried out her term in gaol. Caroline pushed away her untouched tea, angered that Stefan had lied to her and didn't read the rest of the article.

Maggie pulled the article towards her once Caroline had gone outside to see what the fuss was about. She read a confession from Cry-Baby, addressed to her attention: "I love Caroline, if that's a crime, I stand convicted." Maggie left her chair, realizing what must have happened. She found Caroline showing off her engagement ring and she heard the anger in her voice as she replied to a journalists question regarding whether she had anything to say to Cry-Baby. "I think you're a liar, and a cad, and I spit on your tears!" Tyler grinned, taking her chin in his bruised hand and she wrapped her arms around his neck, smiling when he kissed her. Maggie let the newspaper drop from her hands, knowing now it was too late.

* * *

"What's on your face, blubber boy?" A Guard laughed at the sight of Stefan's tattooed tear below his left eye. Stefan ignored him as he crossed over into the cell where they were shaving prisoner's heads. He remembered having the tear done by his mate, Marcel, who like many of his friends stood by him, despite the rumours Elena made up about him fathering her child. Stefan had been heartbroken by Caroline's decision to marry Tyler and wished he could talk to her, but she refused to come anywhere near him.

"Real tears wash away, this one's for Caroline, and I want it to last forever." He had said to Marcel. Stefan knew his family weren't going to forget what he did for them. Taking the blame meant that Rebekah and Damon weren't in jail and were plotting his escape. Damon held onto Rebekah's hand as they ran across the grass and domineered a helicopter, flying it over the prison and into the courtyard. Stefan heard the chopper and so did the guards, putting down their razors and radioing a security breach. Marcel told him to run, and shoved his shoulder against the nearest guard.

Whilst all this was happening, Maggie had gone to the orphanage and bought Sarah's children, intending on doing the right thing and apologising for the Square's inhumane treatment of people. She told them her donation would be the last, if they did not change their act. Maggie met with Lily Salvatore, who gave her a parting skull broach in thanks. Elena who was not pregnant, only devious, had diverted her attention from Cry-Baby to Caroline's fiancé.

Maggie did not approve of violence in general, but she grew tired of Elena's behaviour and felt she needed to do something to stop Caroline from marrying the wrong man. "You may be a square Elena, but you're still trash. And You Tyler, you promised to look after by baby, but instead you put her in danger countless times and encouraged others to discriminate, when you should be making amends..."

Caroline played with her engagement ring while Tyler gaped in response to Maggie's tirade. Lily Salvatore smiled, adjusted her unusual hat, while Caroline saw Sarah and Matt, holding hands with the twins. "I regret not listening to my granddaughter when she had found somebody who made her happy. It doesn't matter where you live, so long as your heart is pure. I have realized these people can teach us many things, if we let them. I pity anyone who does not open their eyes, and see the beauty that lies before them, and of the lifelong friendships we can make."

Caroline furrowed her brow, seeing Katherine, Rebekah and Damon appear before her. Her heart thumped at their intervention, and she saw Tyler looking back at her in shock. Elena gave Caroline a look of jealousy and flipped her hair over her shoulder, readjusting her boobs and flashing them in Tyler's face. Caroline bit her lip, torn between what was right and what was wrong.

"And lastly, Caroline, I want to ask you, to give you the choice I never had, to marry the person you love, and not because it's convenient. Come with me to see Cry-Baby and give him another chance."

Caroline stood in a vibrant red dress on the bonnet of Stefan's car, tapping her hands against her leg. She beamed up at the jailhouse, ready to sing her heart out, for this had been her idea, to support Stefan and tell him that she was sorry, and that she should never have believed anything that came out of Elena's mouth. Katherine smirked, dinging her triangle, and keeping the tempo while Rebekah smirked at Damon, and re-applied her lipstick. Sarah gave Caroline a smile and a nod, and Matt entertained the twins, keeping tabs on Sarah and her unborn child.

_"Please Mr Jailer, won't you let my man go free? Please, Mr Jailer, let an honest man , go free..." _

Caroline sat on the back of Stefan's motorbike and buried her chin against his shoulder. She kissed him just beneath the ear and held his attention, promising him, he was stuck with her forever.

"Care to tell me how you managed to bribe the magistrate into letting me go?" he grinned.

"Grams agreed to go on a date with him, turns out she's quite an influential woman," Caroline said.

**A/N: Please review! I had fun converting this one, and yes I'll be making a trailer to accompany it.**


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